Jennifer-
Welcome back! We love your questions.
I am so excited you are looking to purchase an Annual Pass! We absolutely love ours.
When you book a Magic Your Way Package, you are purchasing tickets and a resort hotel reservation. The value of this package depends on the length of stay, number of days in the parks and the specific Disney property.
I would definitely upgrade your ticket before using it which will get you the most value. There are several locations where Guests can upgrade Magic Your Way Tickets such as Guest Relations at all theme parks, 2 locations at Downtown Disney and by calling 407-WDISNEY. Resort concierges and lobbies current do not offer this service. My best advice is to contact your Walt Disney World Resort travel specialist prior to your trip to evaluate the advantage of upgrading before you leave and working out the room details with your new Annual Pass.
The best news is that with an Annual Pass you get special pricing on many Disney services. The current
Annual Passholder benefits for 2015 include discounts on rooms, dining plans, discounts at specific restaurants, merchandise, recreation, free theme park parking, tours and the flexibility to visit any theme park when you want. Your current resort rate may be the best value but I would ask. There may even be a better Annual Passholder room promotion for your trip. I am using my Annual Pass to receive a discounted room at Disney's Wilderness Lodge in February. We cannot wait!
It truly is wonderful and you are going to love it.
Wishing you many Magical Memories with your Annual Pass!
Jason